Who does he think he is?

Dan Winslow, a veteran Massachusetts Republican turned freshman state rep, is shaking up the State House with a flurry of policy proposals and a scathing critique of the Beacon Hill status quo.

it’s an early March afternoon and a gaggle of reporters are waiting outside the House chamber. The focus of their interest finally steps out and obliges the group. He and the governor, whatever their differences, both agree on the importance of unions to the public workforce, he says. It shouldn’t have been a remarkable scene. But this was not the House Speaker holding forth on the issue of the day or even one of his leadership deputies or a committee chairman. The man of the moment was a freshman state rep, and a lowly Republican to boot.

On Beacon Hill, freshman reps are expected to be seen but not heard. And Republican freshmen are barely seen at all. But Dan Winslow, a judge-turned-Romney-chief-counsel-turned-Republican lawmaker, is seen every­where these days. And heard. He’s organizing press conferences, calling in to radio shows, appearing on television, and jousting with the lefties on Blue Mass Group. He’s on Twitter, playfully likening the House Speaker and Senate President to North Korean dictator Kim Jong Il. And it seems like he’s getting himself quoted in a news story every day.

Winslow’s antics are in some ways a throwback—not to a musty time best forgotten but a period perhaps worth reclaiming. In the 1970s and 1980s, the culture of Beacon Hill was more open. Reformers on both sides of the aisle gained traction and climbed the political ladder on the power of their proposals. That’s how Michael Dukakis, Barney Frank, Andrew Card, and Andrew Natsios all rose within and, ultimately, out of the Legislature. The State House’s power structure is far more rigid these days. Com­­mittee deliberations are largely perfunctory. The Speaker and Senate president set the legislative agenda, and the party faithful either follow along or dissent at their own peril. It’s not a model that Winslow is quietly abiding.

At today’s installment of the Dan Winslow Show, an Associated Press reporter has some questions about a Scot Lehigh column in that morning’s Boston Globe, one that dubbed a Winslow proposal to rein in collective bargaining “the most interesting notion I’ve heard during the pyrotechnics about public-employee unions.” The seeds for the column may have been planted a few days before, when Winslow used the hyperventilation over Wisconsin Gov. Scott Walker’s union-busting to crash onto Blue Mass Group, the left-leaning political blog. He pitched a bill that would crib a 1980s-vintage law Barney Frank sponsored to rein in union costs at the MBTA, take that system statewide, and maybe save a few hundred million dollars along the way. Winslow argued his case to the lefty netroots online, and then offered to hash out the state’s full range of maladies with them, over dinner and a moderate quantity of drinks. In the weeks that followed, Winslow’s collective bargaining proposal led to a union-led occupation of his office and to a State House rally at which the freshman lawmaker was labeled a “yahoo,” a “right-wing idiot,” and an “asshole,” and threatened with expulsion to Rhode Island.

All of this—the media spotlight, the bold ideas, and the relentless gossip that follows—is stuff Beacon Hill hasn’t seen from a new lawmaker in decades. But Winslow isn’t just another legislative newbie. He is the former presiding justice at the Wrentham Dis­trict Court. He served as chief legal counsel to former governor Mitt Rom­ney, and was the top lawyer for Scott Brown’s successful Senate campaign. He could easily be working in Wash­ing­ton, DC, right now or sitting in a downtown office tower, charging several hundred dollars per hour for legal work. Instead, Winslow left his partnership at the white-shoe law firm Duane Morris to run for the House seat Brown once held. His immediate reward was a windowless office in a dark corner of the State House basement, a cubby widely believed to be one of the building’s worst workspaces.“His enthusiasm is not contrived. He’s always asking, ‘Why don’t we do this?’ It never starts with ‘We can’t do this because…'”It’s difficult for a pen of concrete and laminate wood paneling to contain Winslow. From his little subterranean office, Winslow is cranking out legislation and carving out a unique place for himself—that of the defiant cage-rattler—in the largest freshman class Beacon Hill has seen in two decades. Whether he will end up regarded as blunt-talking flash-in-the-pan or a model for a more free­wheeling style in the Legislature is unclear. But Winslow has the nerve to think that ideas should matter to the legislative process, and he’s going put that notion to the test.

“I don’t need the job,” says Winslow, who hails from an old-line Yankee family and evinces an air of noblesse oblige without the stuffy trappings. “If decent, honest, and hard-working people don’t get involved in government, government won’t be decent, honest, and hard-working. If good people stand on the sidelines, our democracy will devolve to the lowest common denominator of talent and motive. And I refuse to do that.”

“His enthusiasm is not contrived,” says Daniel Haley, a Boston attorney and former Romney aide who worked with Winslow on Brown’s Senate campaign. “He’s exactly the same one-on-one as he is when 10 people are standing around him. He’s always asking, ‘Why don’t we do this?’ It never starts with, ‘We can’t do this because….’ It’s always reasons why something can be done, should be done.”

Robed reformer

Much of Winslow’s career has been spent behind the scenes, first as a lawyer for the Massachusetts Republican Party, and later as a gubernatorial aide. He led the GOP’s challenges to legislative redistricting following the 1985 and 1990 Censuses, and sued the Governor’s Council to overturn a string of judicial confirmations in the last days of the Dukakis administration. He was Gov. Bill Weld’s choice to take over the state party chairmanship in 1992 (he was outmaneuvered in that contest), and served as legal counsel during Romney’s 1994 campaign against Ted Kennedy.

Winslow’s family pedigree stretches back to the early days of the Plymouth Colony (an uncle far up the family tree arrived on the Mayflower), but the married father of three lacks the old money and political lineage of the Cabots and Lodges. Winslow’s father fought in Korea, then attended UMass Amherst on the GI bill and settled there. Winslow, who is 52, grew up in Amherst, and wound up in Norfolk after graduating from Tufts and Boston College Law School.

Winslow’s name was floated twice in the early 1990s as a possible pick for US Attorney. He was named to the state bench in 1995, after Weld’s reelection. He gave up that lifetime post in 2002, to join the Romney administration as the governor’s chief legal counsel. Winslow left the Romney administration in early 2005, becoming a partner at the law firm Duane Morris; he’s now a senior counsel at Proskauer Rose, where his practice includes litigation and corporate strategy services. But politics is in his blood, and along with his legislative duties he remains employed as the Brown campaign’s counsel. “When you run, the first call you make is to Dan,” says Charley Man­ning, a Republican political consultant. “He knows more than anybody else—all the arcane rules.”

During Winslow’s seven years as a judge, he won some tabloid notoriety by proposing that repeat drunken drivers have orange warning stickers affixed to their vehicles. (He tested the idea by placing one on the back of his Volvo, and then studying drivers’ reactions.) He also spearheaded an effort to expand jury trials beyond Norfolk County’s Quincy and Dedham courthouses. The Wren­tham courthouse, how­ever, wasn’t built to accommodate juries. Elissa Flynn-Poppey, a lawyer who in­terned for then-Judge Winslow, recalls him arriving early and in his robe, moving around courthouse furniture.

But the biggest stir he caused while on the bench was among his own judicial brethren. Winslow won the Pioneer Institute’s 1998 Better Government Com­petition for a paper that decried the judiciary’s case management system. That paper invited stiff blowback from judges who perceived personal criticism in Win­slow’s analysis. He was also criticized for suggesting that judicial funding should be tied to courthouse caseloads —a challenge to the Legislature and to individual judges’ political power. While with Romney, he made the level-funding of the judicial budget contingent upon the collection of $40 million in fees and fines, and drew a sharp rebuke from the chief justice of the Supreme Judicial Court for his troubles.

Now, Winslow notes, several of his case management reforms have been implemented, courthouse budgets are allocated based on caseloads, and Gov. Deval Patrick has increased the judiciary’s fee collection target to $47 million (to plaudits from the SJC). The lessons are twofold, he says. One, “the judiciary is even more hidebound than the legislative process,” he says, so the House won’t be the toughest institution he has taken on. And two, “if you put your head down and you’re willing to do the work, and weather the barbs and arrows, you can get a lot done.”

Marriage man

The governor’s chief legal counsel is normally not a position that generates publicity. But that mission was thrown for a loop in late 2003, when the SJC’s Goodridge decision declared the prohibition of same-sex marriages unconstitutional. Rom­ney was an ardent opponent of same-sex marriage, and his national political ambitions were clear, but it was up to him to enforce Goodridge. Winslow became the administration’s point man on the issue, and its public face.

Citing attorney-client confidentiality, Winslow won’t discuss the administration’s internal response to Goodridge. However, the moves Winslow made publicly, in Romney’s name, drew praise from gay advocates, and stinging criticism from the right. Winslow appeared at a state convention of justices of the peace, and told them they could not refuse to perform same-sex marriages. He also traveled the state, training municipal clerks on the administration of same-sex marriages.

“He worked with an administration that was hostile to equality, and in that hostile environment, he managed to quietly effectuate changes on behalf of marriage equality,” says Arline Isaacson, co-chair of the Massachusetts Gay and Lesbian Political Caucus.

Winslow, who describes his personal politics as “socially tolerant and fiscally prudent,” downplays that interpretation. He says town clerks and justices of the peace took the same oath Romney did, and his legal guidance to them was simple—follow the law when you agree with it, and follow the law when you don’t.

There was spin that Romney was backing away and softening his position, and that was not the case,” Winslow says. “The governor had a choice. He could be like George Wallace and block the entrance to the college. And he was criticized for not doing that. He did the lawful thing. I think it bespoke his integrity.”

Much has been made of Winslow’s exit from the Romney administration. Some Beacon Hill wags believe there was a split between the two men in the aftermath of Goodridge, pointing to the fact that Romney replaced Winslow with a former Connecticut lawmaker who had sponsored a defense of marriage act. Others say Winslow showed too much ambition and independence, and was too cozy with the press, for Romney’s liking. Beacon Hill watchers note that Romney recently gave $5,000 to union-busting Wisconsin Gov. Scott Walker, but he never contributed to Winslow’s legislative campaign. Winslow simply says his plan was to serve two years on Beacon Hill and then return to the bench.

Depending on whom you ask, when Winslow’s time in the governor’s office was over, Romney was either unable or unwilling to steer Winslow through a repeat judicial confirmation by the Governor’s Council. At the time, Governor’s Councilor Christopher Iannella told the Globe votes were lining up against Winslow because “there is a sense that [Romney’s staff] feel they are better than us.” Iannella shrugs that off today. “It’s always rocky with everyone,” he says. “That was so long ago, I don’t know why they pulled his name.”

But Winslow is convinced there was an anti-Romney agenda at work. “There was a real negative energy level in the building against the governor, against his senior team, and I was it,” he says. “I wasn’t convinced I would be confirmed, so I asked the governor not to nominate me.”

GOP pragmatist

The 2010 election cycle was supposed to be a breakthrough year for Massachusetts Republicans. Scott Brown’s shellacking of Attorney General Martha Coakley gave the party a new base of volunteers and activists, energized downbeat town committees across the state, and drew out dozens of new candidates. The GOP challenged the state’s Demo­cratic establishment across the board. And they suffered stinging defeats at nearly every turn, including the governor’s race, where Charlie Baker, long the Republicans’ next great hope, fizzled out. The party actually lost a seat in the state Senate, reducing its caucus to four members in a body of 40.

Those shortcomings leave the House as the Repub­li­cans’ last and only outlet for influencing state policy for the next two years. November’s election doubled the GOP’s numbers in the House, as Republican candidates knocked off 11 incumbent Democrats and claimed four open seats previously held by Democrats. Winslow is one of 20 freshman Republican reps on Beacon Hill. The turnover in the Legislature was so great that House leaders had to move the bullpen, normally a fourth-floor holding pen for new lawmakers, to two large hearing rooms in the State House basement.

Even with their November gains, Republicans still only control 20 percent of the seats in the House. However, Massachusetts has one of the nation’s least competitive state legislatures, and any turnover tends to spawn uncertainty. November’s election “opened up the majority to the idea that they are vulnerable,” says Brad Jones, the Republican House minority leader. “People are hearing footsteps. The Speaker isn’t going to bring up votes that he thinks might jeopardize his members.”

House Speaker Robert DeLeo has already vowed to close a more than $1.5 billion budget gap without tax increases. He has also begun likening new fees, such as an expansion of the bottle bill, to taxes. He’s fending off the Republicans while fighting on their fiscal turf.

The defensive stance adopted by House leadership should benefit a legislator like Winslow, who campaigned largely on fiscal issues. A good chunk of the freshman rep’s proposed legislation is aimed at lowering costs and boosting the volume of cash in the state’s economy. Win­slow has filed legislation that would allow residents to write off sales tax expenditures on their income tax claims; establish free enterprise zones in municipalities; create a home refinancing guarantee under Mass­Housing; and allow municipalities to bond out Community Preser­vation Act revenue through the state treasury, thereby slashing administrative costs. He believes the governor’s office should aggressively target entitlement fraud, and he wants to push the forward-funding of labor contracts on the municipal level. Then, of course, there’s that proposal to expand management rights to local and state employers.

These are clearly the proposals of a guy who ran with an R next to his name on the ballot. Even so, Winslow isn’t a GOP caricature. He labels himself an environmentalist, and is the only Re­pub­­lican cosponsor of the expanded bottle bill. During the campaign, he rode his bicycle door to door, rather than drive. (He also used the bike to film a campaign video spoofing Brown’s famous truck ad.)

“When he was in the Romney administration, he wasn’t perceived as an ideologue,” says David Guarino, a veteran Beacon Hill operative. “He was viewed as somebody who could be worked with.” As for Winslow’s early moves in elected office, Guarino says the amount of legislation Win­slow is now pursuing, and the traction he’s getting, are “virtually unheard of” for a freshman. He’s getting that traction, in part, because Winslow is relentless about putting his ideas in front of people. He returns reporters’ phone calls, and when he does, he says something interesting. He’s on Facebook and Twitter, even though they get him in trouble sometimes (like that North Korea crack, or a lead-balloon joke he Tweeted about how a global warming symposium had been snowed out).

And then there’s Blue Mass Group. Winslow began posting on the website, under a pseudonym, in 2006. He outed himself during his legislative race, and he’s currently the only legislative Republican engaging the liberal-leaning site. “He’s been persistent about participating, and he’s always saying something constructive and interesting,” says David Kravitz, one of Blue Mass Group’s editors. “He doesn’t do drive-by posts. He’ll come back and answer some really pointed questions. He’s really using the site as a source of dialogue, rather than a dumping ground for press releases.”

Map-making alliances

For all his optimism about the ability to bring good ideas to the legislative arena, however, in the most far-reaching political fight happening on Beacon Hill right now, Winslow is participating as a civilian, not as a legislator.

A bipartisan advocacy group, Fair Districts Mass, headed by longtime GOP gadfly Jack E. Robinson, has retained Winslow the lawyer to champion its cause in the upcoming redistricting battle. That means Winslow the lawmaker will recuse himself from redistricting deliberations at the State House. He will vote up or down on the House’s new legislative map, but he won’t be involved with state Rep. Mike Moran’s map-making committee. Instead, he’s laying the groundwork for a possible federal lawsuit challenging Moran’s maps.

“Redistricting is, ultimately, an exercise in incumbent protection,” Winslow says. He wants to wipe the current legislative map clean, and believes that wouldn’t happen if he were working as the Republican Party’s redistricting point man, as he did following the 1985 and 1990 Censuses. “There’s always this disconnect between incumbent protection and party growth,” he says. Winslow says Fair Districts Mass will push for what he calls fair, constitutional districts—districts that open up Congress and the State House to new challengers from both political parties. In other words, Winslow could wind up angering not only Democrats but fellow Republicans as well.

“I’m of the view that the whole issue of partisanship is getting a little old,” he says. “I don’t like the notion that you lose because I win. Redistricting is the best means for a political paradigm shift, and if there’s ever a state in need of a paradigm shift, it’s ours.”

The group’s main focus will be the creation of a majority-minority congressional district anchored in Suffolk County, and compact, logical districts throughout the rest of the state. Such an approach would drastically alter the current congressional district boundaries (Massa­chusetts is already losing one congressional district in this redistricting round) and open up electoral opportunities for Repub­licans outside Suffolk County. That’s what happened after the 1990 Census, when Win­slow helped push new districts that ultimately led to the election of two Repub­lican congressmen, Peter Blute and Peter Torkildsen, and competitive contests on the South Shore and in the Merrimack Valley.

“He’s playing the hand that works for Republicans and works for min­orities,” says Joyce Ferriabough-Bolling, whose Black Political Task Force partnered with Winslow and state Republicans to influence the new legislative maps that followed the 1990 Census. Winslow got four competitive congressional districts, and Ferriabough-Bolling got strong minority voter influence over the Eighth Con­gres­sional seat currently held by Michael Capuano. “I don’t see him as a soldier of fortune for diversity rights,” she says. But Ferriabough-Bolling thinks he was also happy to advance that goal. “He’s for minority and Republican [advancement]—he believes in both,” she says.

No time to lose

Winslow called his first press conference as a state rep weeks before be was even sworn in. He figured most people were focused on shopping in the last few days before Christmas, which would make it as good a time as any to kick off a debate about lowering the sales tax. So on the Wednesday before Christmas, on an afternoon when the State House was emptying for the end-of-year break, a handful of newly-elected Republicans called a press conference outside the House minority leader’s office and announced their intention to push for a sales tax credit in the upcoming legislative session. The freshmen, led by Winslow, said they would be issuing $2 billion worth of economic growth and cost-cutting proposals in the coming months, and this was the opening shot.

A handful of reporters listened, scribbled notes, and then asked a question: Where was the minority leader, Brad Jones? Why were the freshmen calling this presser on their own? The sight of four freshmen legislators (who hadn’t even been sworn in yet) talking shop and issuing press releases was so rare that it was noteworthy. As far as Winslow is concerned, it shouldn’t be.

“I think the Legislature hasn’t lived up to its fullest institutional potential as a place for debate and discussion, as an incubator for ideas,” he says.

Winslow has already pledged to serve three terms, at most. The self-imposed term limit “lights a fire under me,” he says. If he were on a 20-year plan, he says, he wouldn’t feel as much pressure to get ideas to the House floor.

“I talk to folks who tell me they’ve been here for 24 years,” Winslow says. “Well, respectfully, what are you going to do in the next two that you haven’t done in the previous 24? The people who have been there the longest, you’ve never heard of, because they’ve never done anything! Why are they there, other than to consume oxygen and to pander to the special interests that sustain them in their roles?”

He pauses. The man of big ideas can also throw a sharp elbow, sometimes before he even realizes it. “They’re all nice people,” he continues. “When they read this, they’re all going to be mad at me. That’s fine.”

His legislative colleagues have more than the occasional barb to stew over. In his constant churning out of proposals and policy views, Winslow is working the mainstream press and social media channels relentlessly (he now boasts more than 1,000 Facebook “friends”). It sometimes has the feel of shameless self-promotion, and some of Winslow’s colleagues undoubtedly see it that way. But in a body that has become so sclerotic with top-down authority, a media-savvy outside strategy like Winslow’s might be the only way to get traction on an issue.

“The easiest thing to do in government is nothing,” Winslow says. “People expect nothing of you in government. They’ll not criticize you for doing nothing, because that’s the level of expectation. It’s when you stick your head up and you start putting ideas out, that’s when you get the criticism and the pushback and the pressure.”

That pushback and pressure are already mounting. It’s not because any one of Winslow’s 19 bills has angered some great and powerful lobby on Beacon Hill. It’s the pace he’s working at, his refusal to refuse comment, and his ever-growing pile of press clips—that’s what’s catching his colleagues’ attention.

Legislators and staff have taken to asking reporters what office Winslow is running for. There is no shortage of theories. Some believe he’s angling for governor, or attorney general, or secretary of state. Others believe he wants to depose Brad Jones and seize control of the House Republican caucus. Still others think it’s about revenge—those goons on the Governor’s Council wouldn’t let him back on the bench, so now he’s going to make life miserable for every Democrat on Beacon Hill.

Meet the Author

Paul McMorrow

Associate Editor, CommonWealth

About Paul McMorrow

Paul McMorrow comes to CommonWealth from Banker & Tradesman, where he covered commercial real estate and development. He previously worked as a contributing editor to Boston magazine, where he covered local politics in print and online. He got his start at the Weekly Dig, where he worked as a staff writer, and later news and features editor. Paul writes a frequent column about real estate for the Boston Globe’s Op-Ed page, and is a regular contributor to BeerAdvocate magazine. His work has been recognized by the City and Regional Magazine Association, the New England Press Association, and the Association of Alternative Newsweeklies. He is a Boston University graduate and a lifelong New Englander.

About Paul McMorrow

Paul McMorrow comes to CommonWealth from Banker & Tradesman, where he covered commercial real estate and development. He previously worked as a contributing editor to Boston magazine, where he covered local politics in print and online. He got his start at the Weekly Dig, where he worked as a staff writer, and later news and features editor. Paul writes a frequent column about real estate for the Boston Globe’s Op-Ed page, and is a regular contributor to BeerAdvocate magazine. His work has been recognized by the City and Regional Magazine Association, the New England Press Association, and the Association of Alternative Newsweeklies. He is a Boston University graduate and a lifelong New Englander.

On the topic of any political ambitions he may harbor, the usually loquacious lawmaker is a man of few words. “I’m running for reelection in 2012,” he says.

Maybe Winlsow does have his eye on higher office. Or maybe the very fact that there’s so much gossip equating legislative vigor with power lust just means Winlsow’s critique of Beacon Hill is dead-on.